FeCl3-catalyzed oxidative decarboxylation of aryl/heteroaryl acetic acids: preparation of selected API impurities. Issue 41 (15th October 2020)

• Record Type: Journal Article
• Authors: Gangadurai, Chinnakuzhanthai; Illa, Giri Teja; Reddy, D. Srinivasa
• Is Part Of: Organic & biomolecular chemistry. Volume 18:Issue 41(2020)
• Page Start: 8459
• Page End: 8466
• Publication Date: 2020-10-15
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/d0ob01790f
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : An iron catalyzed one-pot, environmentally benign protocol for the oxidative decarboxylation of aryl/heteroaryl acetic acids to synthesize corresponding carbonyl compounds and five important API impurities is described. Abstract : There is an ever-increasing demand for impurity compounds for use in impurity profiling as regulatory agencies seek information during registration. Herein, we report the FeCl3 -catalyzed oxidative decarboxylation of aryl- and heteroaryl acetic acids to the corresponding carbonyl compounds. A variety of useful aldehydes and ketones were prepared in a simple one-pot transformation by employing an environmentally benign, low-cost, and readily available iron salt. The utility of this method has been demonstrated by preparing five valuable API impurities including a multi-gram-scale synthesis of ketorolac impurity B for the first time.